Water → HCID 90051806, compound

HRID 2284803Notes

Reaction equation

HRID 2284803 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([CH:15]=O)=[CH:13][N:12]=[C:11]([S:17][CH3:18])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:20][OH:21].C(OCC)(=O)C.O>N1C=CC=CC=1>[CH2:1]([O:8][C:9]1[C:14]([CH:15]=[N:20][OH:21])=[CH:13][N:12]=[C:11]([S:17][CH3:18])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 443297Hydroxyamine hydrochlorideHCID 90052172HCID 90052172, compound

Product 1

HCID 90051806HCID 90051806, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-(benzyloxy)-2-(methylthio)pyrimidine-5-carbaldehyde (S20, 223 mg) in pyridine (4.0 mL), hydroxylamine hydrochloride (95.8 mg) was added at room temperature, and the mixture was stirred at room temperature for 2 hours. To the reaction mixture, ethyl acetate and water were added. The organic layer was separated, washed successively with water and saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 4-(benzyloxy)-2-(methylthio)pyrimidine-5-carbaldehyde oxime (S21, 233 mg).

Workup

  1. customThe organic layer was separated
  2. washwashed successively with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c01e7980eab44045b6626aa0e7580e48
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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